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Biotransformation of natural polyacetylene in red ginseng by Chaetomium globosum

  • Wang, Bang-Yan;Yang, Xue-Qiong;Hu, Ming;Shi, Li-Jiao;Yin, Hai-Yue;Wu, Ya-Mei;Yang, Ya-Bin;Zhou, Hao;Ding, Zhong-Tao
    • Journal of Ginseng Research
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    • v.44 no.6
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    • pp.770-774
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    • 2020
  • Background: Fermentation has been shown to improve the biological properties of plants and herbs. Specifically, fermentation causes decomposition and/or biotransformation of active metabolites into high-value products. Polyacetylenes are a class of polyketides with a pleiotropic profile of bioactivity. Methods: Column chromatography was used to isolate compounds, and extensive NMR experiments were used to determine their structures. The transformation of polyacetylene in red ginseng (RG) and the production of cazaldehyde B induced by the extract of RG were identified by TLC and HPLC analyses. Results: A new metabolite was isolated from RG fermented by Chaetomium globosum, and this new metabolite can be obtained by the biotransformation of polyacetylene in RG. Panaxytriol was found to exhibit the highest antifungal activity against C. globosum compared with other major ingredients in RG. The fungus C. globosum cultured in RG extract can metabolize panaxytriol to Metabolite A to survive, with no antifungal activity against itself. Metabolites A and B showed obvious inhibition against NO production, with ratios of 42.75 ± 1.60 and 63.95 ± 1.45% at 50 µM, respectively. A higher inhibitory rate on NO production was observed for Metabolite B than for a positive drug. Conclusion: Metabolite A is a rare example of natural polyacetylene biotransformation by microbial fermentation. This biotransformation only occurred in fermented RG. The extract of RG also stimulated the production of a new natural product, cazaldehyde B, from C. globosum. The lactone in Metabolite A can decrease the cytotoxicity, which was deemed to be the intrinsic activity of polyacetylene in ginseng.

Physicochemical Properties of Red Ginseng on Storage Condition of the Fresh Ginseng (수삼의 저장조건에 따른 홍삼의 이화학적 특성)

  • Kim, Chun-Suk;Jung, In-Chan;Kim, Se-Bong;Yang, Deok-Chun
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.1
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    • pp.52-56
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    • 2005
  • This study was compared the quality of red ginseng and characteristic changes of physicochemical properties according to the storage period (non storage, two days, six days, eight days, ten days) and store temperature $20^{\circ}C, \;34^{\circ}C,\;-10^{\circ}C)$. The water content of the fresh ginseng has a tendency to decrease as storage time increases. When we store the fresh ginseng for 10 days, the ideal storage temperature is considered to be $34^{\circ}C$ degrees. The amount of total nitrogen has a tendency to increase more than that of no storage as storage period approaches to 10 days. In the storage temperature, the amount of total nitrogen has a tendency to increase in the order of 1) room temperature, 2) freezing storage, 3) cold storage more than no storage. Cold storage has larger contents of total phenolic compounds than room temperature and freezing storage according to storage temperature. When we analyze the changes of a relative density of eight elements, ginsenoside $Rb_1,Rb_2,Rc,Rd,Re,Rg_3,Rg_1\;and\;Rg_2$ in red ginseng's saponin Rf according to storage condition, the relative density of $Rb_1\;and\;Rg_1$ against Rf diminishes in each storage condition as storage time increases. And it is also thought that density change of ginsenoside appears because of the materials, and change tendency according to storage condition is not clear. From functional nature on the evaluation of the quality, taste and fragrance of red ginseng according to storage district, it is evaluated that it is most recommendable for red ginseng to be transported and stored in $3{\sim}4$ degrees to keep its best condition.

Synergistic Effects of KH-red Ginseng/chlorella on the Endurance Capacity and Immune Enhancing in Forced Swimming Tested Mice

  • Choi, In-Young;Lee, Ji-Hyun;Kang, Tae-Hee;An, Hyo-Jin;Kim, Su-Jin;Moon, Phil-Dong;Kim, Na-Hyung;Myung, Noh-Yil;Yang, Deok-Chun;Kang, In-Cheol;Choi, Young-Jin;Kim, Min-Ho;Um, Jae-Young;Hong, Seung-Heon;Kim, Hyung-Min;Jeong, Hyun-Ja
    • Food Science and Biotechnology
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    • v.18 no.6
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    • pp.1351-1357
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    • 2009
  • KH-red ginseng/chlorella (KH-RG/C) is the mixed material of the Korean red ginseng powder (Panax ginseng, 75%) and extract of Chlorella vulgaris (25%). To evaluate the effects of KH-RG/C on endurance capacity and immune regulation, the forced swimming test (FST) was conducted. The immobility time in the FST was significantly decreased in KH-RG/C treated group compared with the DW-treated group at the 3 and 10 days, respectively. In the analysis of the blood biochemical parameters, KH-RG/C treatment significantly increased the glucose level. However, the lactic dehydrogenase level decreased. Although KH-RG/C increased aspartate aminotransferase, it was not different significantly. And KH-RG/C had no affects in the alanine aminotransferase, and blood urea nitrogen levels. In splenocytes and macrophages, KH-RG/C also did not affect the interleukin (IL)-2, IL-4, and IL-12 production. These results suggest that KH-RG/C may influence to immune regulation through increasing the physical endurance capacity without effect in activation of immune cells.

A Study on the Saponin Contents and Antioxidant Activity of the Ginseng and Extruded Ginseng by Using Different Solvents for Extraction (추출 용매에 따른 인삼과 압출 성형 인삼의 사포닌 함량 및 항산화 활성 연구)

  • Kim, Sung-Hwan
    • The Korean Journal of Food And Nutrition
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    • v.24 no.4
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    • pp.528-534
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    • 2011
  • This study was conducted to investigate the changes in saponin content and antioxidant activity of crude ginseng and extruded ginseng by using different solvent extraction methods. Each of the fractions was first extracted by 80% ethanol followed by ether treatment to remove the lipid components. Water soluble components were separated by ethylacetate and water saturated butanol. Four fraction, including 80% ethanol, ethylacetate, butanol and water were obtained from crude and extruded ginsengs to analyze saponin content and antioxidant activity. Saponin content and antioxidant capacity of each of the four fractions were measured by LC/MS analysis and ORAC(Oxygen Radical Absorbance Capacity) assay, respectively. It was found that a major portion of saponin was present in ethyl acetate and water saturated butanol fractions. When extracted by 80% ethanol, ginsenoside Rb1 and Rg1 were mostly found in crude ginseng, while ginsenoside Re and Rb1 were detected in extruded ginseng. Even though Rh1 and Rg3 were found in a very small quantity in crude ginseng, there was a significant quantity of both in extruded ginseng when extracted by 80% ethanol. Similar tendency was also observed in extruded ginseng fraction when extracted with ethyl acetate and butanol. In crude ginseng, the level of Rg1 was the highest among other ginsenosides upon extraction by ethyl acetate, while Rh1 and Rg3 were predominantly found by employing similar solvent extraction in the extruded ginseng. Also, Rg1, Re and Rb1 were also found in the extruded ginseng with small quantity. Rg1, Re and Rb1 were found in crude ginseng by butanol extraction, while Rb1 and Re were extracted from the extruded ginseng. Overall, there was no difference in the saponin content between crude ginseng and extruded ginseng when extracted by butanol and water, but twice as much of saponin was obtained by 80% ethanol extraction and 6 times more saponin were obtained in ethyl acetate fraction in the extruded ginseng. Antioxidant capacity of crude ginseng as determined by ORAC assay was higher in 80% ethanol(high in many different kinds of biological compounds) and water saturated butanol(high in polar saponin) fractions than the ethyl acetate and water fractions. No difference in antioxidant capacity was observed between crude and extruded ginseng. However, antioxidant capacity of ethyl acetate and water fractions in extruded ginseng was significantly higher than crude ginseng($P$ >0.05). All the fractions in both, crude and extruded ginseng possessed antioxidant capacity and even water fractions that contained almost no saponin had some antioxidant capacity. While determining correlation coefficient between fractions in extruded ginseng by Pearson correlation, it was observed that 80% ethanol fraction was in correlation with ethyl acetate($P$ >0.01) and ethanol($P$ >0.001) and in the case of ethylacetate, correlation was observed only with butanol fraction($P$ >0.05).

Enhancement of Railway Graph for Representing Othogonal Railway Crossing in a Track Network (철도 네트워크에서 직교 교차선로 표현을 위한 선로그래프의 개선)

  • Cho, Dong-Young
    • The Journal of Korean Association of Computer Education
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    • v.6 no.4
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    • pp.61-69
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    • 2003
  • RG(Railway Graph), which is a connected graph structure with the concepts of internal and external edges, is a data structure for representing railway assignments in a track network. In RG, it is possible to represent railway connectivities considering it's forward direction which is impossible in a digraph representation. But with RC, we can not still represent an othogonoal railway crossing in a track network. In this paper, we extend RG using the concept of dummy edge. Using ERG(Extended Railway Graph), we describe a method to consistently represent track network including othogonoal railway crossings, data structure for our ERG, and path allocation algorithm in ERG.

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Changes in Effective Components of Ginseng by Puffing (팽화에 의한 인삼 유효성분의 변화)

  • Kim, Ji-Hye;Ahn, Soon-Cheol;Choi, Sung-Won;Hur, Nam-Youn;Kim, Byung-Yong;Baik, Moo-Yeol
    • Applied Biological Chemistry
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    • v.51 no.3
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    • pp.188-193
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    • 2008
  • This study was conducted to investigate the effect of moisture content and pressure on extraction yield, crude saponins and ginsenoside contents of puffed Korean ginseng. Puffed ginsengs showed relatively higher extraction yield ($50.0{\sim}62.1%$) and amounts of crude saponins ($19.6{\sim}48.8$ mg/g ginseng) than no-puffed ginseng ($37.6{\pm}0.8%$ and $11.0{\pm}1.0$ mg/g ginseng), respectively. The highest extraction yield and amounts of crude saponins were obtained in 8.0% moisture content sample puffed at 10 $kg_f/cm^2$. In HPLC analysis, amounts of measured major ginsenosides (Rb1, Rb2, Rc, Rd, Re, and Rg1) decreased with increasing puffing pressure, yet contents of almost all major gin senosides were higher than control (no-puffed). On the other hand, ginsenoside Rg3 were produced after puffing suggesting that chemical structure of some ginsenosides might be altered during the puffing process. These results indicate that puffing can increase the extraction yield and crude saponin contents and it could influence the ginsenoside composition.

Bioavailability of Fermented Korean Red Ginseng

  • Lee, Hyun-Jung;Jung, Eun-Young;Lee, Hyun-Sun;Kim, Bong-Gwan;Kim, Jeong-Hoon;Yoon, Taek-Joon;Oh, Sung-Hoon;Suh, Hyung-Joo
    • Preventive Nutrition and Food Science
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    • v.14 no.3
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    • pp.201-207
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    • 2009
  • In an effort to improve ginsenoside bioavailability, the ginsenosides of fermented red ginseng were examined with respect to bioavailability and physiological activity. The results showed that the fermented red ginseng (FRG) had a high level of ginsenoside metabolites. The total ginsenoside contents in non-fermented red ginseng (NFRG) and FRG were 35715.2 ${\mu}g$/mL and 34822.9 ${\mu}g$/mL, respectively. However, RFG had a higher content (14914.3 ${\mu}g$/mL) of ginsenoside metabolites (Rg3, Rg5, Rk1, CK, Rh1, F2, and Rg2) compared to NFRG (5697.9 ${\mu}g$/mL). The skin permeability of RFG was higher than that of NFRG using Franz diffusion cells. Particularly, after 5 hr, the skin permeability of RFG was significantly (p<0.05) higher than that of NFRG. Using everted instestinal sacs of rats, RFG showed a high transport level (10.3 mg of polyphenols/g sac) compared to NFRG (6.67 of mg of polyphenols/g sac) after 1 hr. After oral administration of NFRG and FRG to rats, serum concentrations were determined by HPLC. Peak concentrations of Rk1, Rh1, Rc, and Rg5 were approximately 1.64, 2.35, 1.13, and 1.25-fold higher, respectively, for FRG than for NFRG. Furthermore, Rk1, Rh1, and Rg5 increased more rapidly in the blood by the oral administration of FRG versus NFRG. FRG had dramatically improved bioavailability compared to NFRG as indicated by skin permeation, intestinal permeability, and ginsenoside levels in the blood. The significantly greater bioavailability of FRG may have been due to the transformation of its ginsenosides by fermentation to more easily absorbable forms (ginsenoside metabolites).

Bioconversion of Ginsenosides in Red Ginseng Extract by Saccharomycescerevisiae and Saccharomyces carlsbergensis (홍삼농축액에서 Saccharomyces cerevisiae와 Saccharomyces carlsbergensis에 의한 Ginsenosides의 bioconversion)

  • Jang, Mi;Min, Jin-Woo;Kim, Ju-Han;Kim, Se-Young;Yang, Deok-Chun
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2010.05a
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    • pp.16-16
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    • 2010
  • Ginseng(Panax ginseng C.A. Meyer) is reported to have many pharmaceutical activities. The minor ginsenosides(Rd, Rg3, Rh2 and compound K) display pharmaceutical properties superior to those of the major ginsenosides. These minor ginsenosides, which contribute a very small percentage, are produced by hydrolysis of the sugar moieties of the major ginsenosides. The pH of red ginseng extracts fermented with S. cerevisiae and S. carlsbergensis decreased rapidly during 3 days of fermentation, with no further significant change thereafter. After 20 days of fermentation, a relatively small difference remained in the acidity of extracts fermented with S. cerevisiae (0.54%) and S. carlsbergensis (0.58%). Reducing sugar in the S. cerevisiae and S. carlsbergensis extracts decreased from 25.86 to 4.54 mg/ml and 4.32 mg/ml glucose equivalents, respectively; and ethanol contents increased from 1.5% at day 0 to 16.0 and 15.0%, respectively, at 20 days. Ginsenosides Rb1, Rb2, Rc, Re, Rf, and Rg1 decreased during the fermentation with S. cerevisiae, but Rd and Rg3 increased by 12 days. Ginsenosides Rb1, Rb2, Rc, Re and Rg1 decreased gradually in the extract with S. carlsbergensis, but Rd and Rg3 were increased at 6 days and 9 days.

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Study on biosynthesis of ginsenosides in the leaf of Panax ginseng by seasonal flux analysis

  • Kim, Dongmin;Han, Jaehong
    • Journal of Applied Biological Chemistry
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    • v.62 no.4
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    • pp.315-322
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    • 2019
  • Seasonal ginsenoside flux in the leaves of 5-year-old Panax ginseng was analyzed from the field-grown ginseng, for the first time, to study possible biosynthesis and translocation of ginsenosides. The concentrations of nine major ginsenosides, Rg1, Re, Rh1, Rg2, R-Rh1, Rb1, Rc, Rb2, and Rd, were determined by UHPLC during the growth in between April and November. It was confirmed total ginsenoside content in the dried ginseng leaves was much higher than the roots by several folds whereas the composition of ginsenosides was different from the roots. The ginsenoside flux was affected by ginseng growth. It quickly increased to 10.99±0.15 (dry wt%) in April and dropped to 6.41±0.14% in May. Then, it slowly increased to 9.71±0.14% in August and maintained until October. Ginsenoside Re was most abundant in the leaf of P. ginseng, followed by Rd and Rg1. Ginsenosides Rf and Ro were not detected from the leaf. When compared to the previously reported root data, ginsenosides in the leaf appeared to be translocated to the root, especially in the early vegetative stage even though the metabolite translocated cannot be specified. The flux of ginsenoside R-Rh1 was similar to the other (20S)-PPT ginsenosides. When the compositional changes of each ginsenoside in the leaf was analyzed, complementary relationship was observed from ginsenoside Rg1 and Re, as well as from ginsenoside Rd and Rb1+Rc. Accordingly, ginsenoside Re in the leaf was proposed to be synthesized from ginsenoside Rg1. Similarly, ginsenosides Rb1 and Rc were proposed to be synthesized from Rd.

The Changes of Physicochemical Characteristics and Quality Stability of Korean Red Ginseng (Panax ginseng C.A. Meyer) Stored over 20 Years (20년 이상 장기저장된 홍삼의 이화학적 특성변화 및 품질안정성)

  • Kwak, Yi-Seong;Han, Min Woo;Bae, Bong-Seok;Ahn, Nam-Geun;Yu, Hye Young;Park, Chol-Soo;Baeg, In-Ho;Cho, Byung-Gu
    • Korean Journal of Pharmacognosy
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    • v.48 no.4
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    • pp.329-338
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    • 2017
  • This study was investigated the changes of quality stability and physicochemical characteristics of the Korean red ginsengs stored for a long times over 20 years. The Korean red ginsengs were stored for 4 to 22 years in canned packaging with polypropylene film and wooden box at room temperatures. The unusal phenomena such as discoloration and pin hole in packaging were not observed. General bacteria showed the vlaues of below 100 CFU/g, coliform groups and molds were not found in any samples stored for 22 year. Any samples also were not detected in mycotoxins. The contents of moisture, ash and crude saponin were the levels of 10.6~11.1%, 3.8~4.2% and 4.1~4.7% during the whole storage periods, respectively. The contents of maltol, which has been known as characteristic flavour and antioxidant of Korean red ginseng, showed remarkably increasing tendency from 0.10 mg/g for 4 years to 2.53 mg/g for 22 years during the storage. The contents of AFG (arginyl-fructosyl-glucose), arginine and free sugar were slightly decreased. Acidic polysaccharide and ginsenoside were not changed significantly during the storage periods. The contents of acidic polysaccharide and total ginsenosides were the 75.1~76.3 mg/g and 15.1~16.6 mg/g, respectively. The sums of ginsenoside-Rg1,-Rb1 and -Rg3s were the ranges of 9.3~9.9 mg/g and PD (ginsenoside-Rb1, -Rb2,-Rc,-Rd,-Rg3s,-Rg3r)/PT (ginsenoside-Rg1,-Rg2,-Re,-Rf,-Rh1) saponin ratios were the levels of 1.4~1.5. These results suggest that Korean red ginsengs stored for long periods show relatively stable quaility stabilities and not significantly changed the contents of ginsenoside and polysaccharide during the storage up to 22 years.